Benzyl Dissolution Questions
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1) "Dissolve .5 g of benzyl in a 5mL of 95% ethanol and cool the solution under the tap to produce a fine suspension. Then add .1 g of sodium borohydride (large excess)."
a. The text refers to 10 mg NaBH4 as a large excess to 50 mg benzi. Do the stoichiometric calculation to show this. Also calculate the theoretical yield of product.
b. Benzil in solution is yellow colored. As the reduction reaction proceeds the yellow color disappear, why is this so?
c. Draw all the products of the borohydride reduction of benzyl using the wedge and dotted line convention, label all asymmetric carbons as R or S and characterize the stereochemistry of each one.*
* Benzil , using reagent NaBH4, will give (1R,2S)-(meso)-hydrobenzoin and (1R,2R) and (1S, 2S)-hydrobenzoin.
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4 questions, including drawing mechanisms, stereochemistry and products for reactions, are answered in Word and .jpeg hand-drawn attachments.
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